2-phenyl-4-(p-methoxyphenyl)-3-buten-2-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-phenyl-4-(p-methoxyphenyl)-3-buten-2-ol
• 英文别名: (E)-4-(4-methoxyphenyl)-2-phenyl-3-buten-2-ol；(E)-4-(4-methoxyphenyl)-2-phenylbut-3-en-2-ol
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: FOSWQIOLFFHYRW-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C-(4-methoxyphenyl)-N-methyl nitrone 在 cathecol 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 151.5h， 生成 2-phenyl-4-(p-methoxyphenyl)-3-buten-2-ol
  参考文献：
  名称：

  Ring-opening of Isoxazolidine Nucleus by Trimethyl Posphate Treatment: Formation of Tertiary Allylic Alcohols via Intermediate 1,3-Oxazinium Salts

  摘要：

  5,5-Disubstituted isoxazolidines undergo ring opening reaction, leading to tertiary allylic alcohols, by sequential treatment with trimethyl phosphate (TMP) and NaH. The reaction proceeds through sequence steps which involve an initial alkylation to isoxazolidinium intermediate, followed by ring expansion to tetrahydro-1,3-oxazine, further alkylation and a Hofmann-like elimination towards the final products promoted by NaH.

  DOI：

  10.3987/com-92-6239

文献信息

• New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis
  作者：Alejandro G. Hernán、Peter N. Horton、Michael B. Hursthouse、Jeremy D. Kilburn

  DOI：10.1016/j.jorganchem.2005.11.031

  日期：2006.4

  prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride reagents have been used in a catalytic Stille coupling cycle and the resin-bound distannanes have been used in atom transfer cyclisations and proved to be much more effective than previously described

  已经制备了新型的与树脂结合的有机锡试剂，包括首次与树脂结合的二甲基锡试剂。还开发了温和的方法，以非常有效地合成树脂结合的二锡烷。与树脂结合的氯化锡试剂已用于催化斯蒂勒偶联循环中，并且与树脂结合的二锡烷已用于原子转移环化中，并被证明比以前描述的与树脂结合的二锡烷更有效。如所期望的，使用树脂结合的锡试剂有助于它们在反应结束时易于去除，因此有机产物中的残留锡水平较低或可忽略不计。但是，树脂结合的二锡烷不能成功地用于钯催化的简单芳基碘化物的锡烷基化反应，这将为芳香族底物的放射性标记提供有用的方法。锡烷基化过程失败的原因尚不清楚，但晶体结构证据表明，与树脂结合的锡原子与相邻的醚氧之间存在高价相互作用，这可能影响锡中间体在锡烷基化序列中的反应性。
• Stille Couplings Catalytic in Tin:  Beyond Proof-of-Principle
  作者：Robert E. Maleczka,、William P. Gallagher、Ina Terstiege

  DOI：10.1021/ja993446s

  日期：2000.1.1

  amenable to reaction in the fluorous phase,8b,9 and offer great potential in the very nonpolar environment of supercritical carbon dioxide.10 Despite such synthetic utility, a historic drawback of the Stille reaction has been its reliance on stoichiometric quantities of toxic, costly, and occasionally unstable organostannanes.11,12 Therefore, we believe a Stille reaction, which is catalytic in tin, would

  Stille 交叉偶联 1 通常涉及钯催化的乙烯基或芳基卤化物与乙烯基锡烷结合形成 1,3 二烯。Stille 反应对大量的官能团具有相当的耐受性，通常以烯烃几何结构的守恒进行，并且对于新形成的 CC σ 键通常具有区域特异性。因此，Stille 反应已被证明可用于天然产物合成、2 新材料的构建、3 杂环制备、4 碳水化合物化学、5 和生物有机研究的支持。6 此外，Stille 偶联与各种新技术非常兼容。它们在组合环境中表现良好，2a,7 在微波辐射下迅速加速，8 已证明适合在氟相中反应，8b，9 并在超临界二氧化碳的非极性环境中提供了巨大的潜力。 10 尽管具有这种合成效用，Stille 反应的一个历史缺点是它依赖于化学计量数量的有毒、昂贵且偶尔不稳定的有机锡烷。 11,12 因此，我们相信在锡中具有催化作用的 Stille 反应会带来相当大的好处。13 这种催化方法的发明提出了几个挑战
• Stille Couplings Catalytic in Tin:  The “Sn−O” Approach
  作者：William P. Gallagher、Ina Terstiege、Robert E. Maleczka

  DOI：10.1021/ja0035295

  日期：2001.4.1

  lle coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is most effective with Me(3)SnCl serving as the tin source. This

  描述了一种一锅串联 Pd 催化的氢化锡烷基化/Stille 偶联方案，用于立体选择性生成乙烯基锡及其随后的结合，仅使用催化量的锡。通过将有机锡卤化物 Stille 副产物再循环回有机锡氢化物，可以用催化量的锡进行氢化锡酰化/交叉偶联序列。这种过程对于作为锡源的 Me(3)SnCl 最为有效。该协议允许将锡需求量减少 94%，同时为各种 Stille 产品保持良好的产量（高达 90%）。此外，由于一个循环需要锡经历至少四次转化，因此在氢化锡烷基化/Stille 序列的过程中，三烷基锡的每个部分都经历了至少 60 次反应。
• Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions
  作者：Scott E. Denmark、Zhigang Wang

  DOI：10.1021/ol0156751

  日期：2001.4.1

  [GRAPHICS]The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.
• Palladium-catalyzed stereoselective hydrostannation of substituted propargyl alcohols with trineophyltin hydride
  作者：María B. Faraoni、Darío C. Gerbino、Julio C. Podestá

  DOI：10.1016/j.jorganchem.2008.02.015

  日期：2008.5

  This paper reports results obtained in a study on the palladium-catalyzed hydrostannation of substituted propargyl alcohols with the bulky trineophyltin hydride (1). The reaction of 1 with 10 propargyl alcohols containing one up to three substituents, was carried out in THF at room temperature leading to the corresponding allylstannanes following in all cases a syn addition stereochemistry. These additions took place in good to excellent yields and, mostly, with a high degree of stereoselectivity. The results obtained suggest that the observed alpha/beta regioselectivity might be ascribed to the steric bulk of the proximal substituents rather than to electronic effects. Full (1)H-, (13)C-, and (119)Sn NMR characteristics are included. (C) 2008 Elsevier B.V. All rights reserved.